1-(tert-butylthio)-1-diphenylsilyloxyethene | 828246-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(tert-butylthio)-1-diphenylsilyloxyethene
• 英文别名: 1-Tert-butylsulfanylethenoxy(dimethyl)silane；1-tert-butylsulfanylethenoxy(dimethyl)silane
• CAS: 828246-09-9
• 化学式: C₈H₁₈OSSi
• 分子量: 190.382
• InChiKey: VKRADYJGYDUICZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(tert-butylthio)-1-diphenylsilyloxyethene 在 三氟甲磺酸三甲基硅酯 、 substituted (S)-oxazaborolidinone 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  通过环状缩醛衍生物的催化对映选择性开环反应对 2-取代的 1,3-丙二醇进行不对称去对称化

  摘要：

  通过使用恶唑硼烷酮催化的环状缩醛衍生物的对映选择性开环反应，以二甲基甲硅烷基乙烯酮 S,O-乙缩醛为关键，2-取代的 1,3 丙二醇的非酶促去对称化导致对映体富集的 3-苄氧基-1-丙醇反应。

  DOI：

  10.1055/s-2005-871937
• 作为产物：
  描述：

  二甲基一氯硅烷 、 S-叔丁基硫代乙酸酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以53%的产率得到1-(tert-butylthio)-1-diphenylsilyloxyethene
  参考文献：
  名称：

  Dimethylsilyl Ketene Acetal as a Nucleophile in Asymmetric Michael Reaction:  Enhanced Enantioselectivity in Oxazaborolidinone-Catalyzed Reaction

  摘要：

  Dimethylsilanyl [Me2Si(H)] ketene SO-acetal 6b is an effective nucleophile that retards the undesirable Si+-catalyzed racemic pathway in the oxazaborolidinone-catalyzed asymmetric Michael reaction. Through the further suppression of the Si+-catalyzed pathway by carrying out the reaction in the presence of 2,6-diisopropylphenol and t-BuOMe as additives, enantioselectivity up to 98% ee could be achieved for a variety of acyclic enones.

  DOI：

  10.1021/ol048071g

文献信息

• Asymmetric Mukaiyama Aldol Reaction of Nonactivated Ketones Catalyzed by <i>allo</i>-Threonine-Derived Oxazaborolidinone
  作者：Shinya Adachi、Toshiro Harada

  DOI：10.1021/ol802087u

  日期：2008.11.6

  Asymmetric Mukaiyama aldol reaction of nonactivated ketones is realized for the first time by using an oxazaborolidinone catalyst derived from O-benzoyl-N-tosyl-allo-threonine. By employing a dimethylsilyl ketene S,O-acetal as a nucleophile, a variety of acetophenone derivatives afford the corresponding tertiary beta-hydroxy carbonyl compounds with high enantioselectivity up to 98% ee.
• Asymmetric Desymmetrization of 2-Substituted 1,3-Propanediols via Catalytic Enantioselective Ring-Cleavage Reaction of Cyclic Acetal Derivatives
  作者：Toshiro Harada、Koudai Shiraishi

  DOI：10.1055/s-2005-871937

  日期：——

  Non-enzymatic desymmetrization of 2-substituted 1,3propanediols leading to the enantiomerically enriched 3-benzyloxy-1-propanols was achieved by using oxazaborolidinone-catalyzed enantioselective ring-cleavage reaction ofthe cyclic acetal derivatives with dimethylsilyl ketene S,O-acetal as a key reaction.

  通过使用恶唑硼烷酮催化的环状缩醛衍生物的对映选择性开环反应，以二甲基甲硅烷基乙烯酮 S,O-乙缩醛为关键，2-取代的 1,3 丙二醇的非酶促去对称化导致对映体富集的 3-苄氧基-1-丙醇反应。
• Dimethylsilyl Ketene Acetal as a Nucleophile in Asymmetric Michael Reaction:  Enhanced Enantioselectivity in Oxazaborolidinone-Catalyzed Reaction
  作者：Toshiro Harada、Shinya Adachi、Xiaowei Wang

  DOI：10.1021/ol048071g

  日期：2004.12.1

  Dimethylsilanyl [Me2Si(H)] ketene SO-acetal 6b is an effective nucleophile that retards the undesirable Si+-catalyzed racemic pathway in the oxazaborolidinone-catalyzed asymmetric Michael reaction. Through the further suppression of the Si+-catalyzed pathway by carrying out the reaction in the presence of 2,6-diisopropylphenol and t-BuOMe as additives, enantioselectivity up to 98% ee could be achieved for a variety of acyclic enones.